US997301A - Manufacture of orthonitrobenzaldehyde. - Google Patents
Manufacture of orthonitrobenzaldehyde. Download PDFInfo
- Publication number
- US997301A US997301A US58577410A US1910585774A US997301A US 997301 A US997301 A US 997301A US 58577410 A US58577410 A US 58577410A US 1910585774 A US1910585774 A US 1910585774A US 997301 A US997301 A US 997301A
- Authority
- US
- United States
- Prior art keywords
- manufacture
- permanganate
- ortho
- neutral
- orthonitrobenzaldehyde
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title description 6
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 title description 4
- 230000007935 neutral effect Effects 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 235000001055 magnesium Nutrition 0.000 description 2
- 229960003390 magnesium sulfate Drugs 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229940091250 magnesium supplement Drugs 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
Definitions
- FRANCE ASSIGNOIRS TO sooIE'rE CHIMIQUE DES UsINEs Du nHoNE, ANCIENNE- MENT GILLIARD, P. MONNET ET CAR-TIER, or rams, FRANCE, A CORPORATION 01 MANUFACTURE OF ORTHONITROBENZALDEHYDEQ Patented July 11, 1911.
- a process for the manufacture of orthonitrobenzaldehyde comprising treatment of a neutral or approximately neutral solution of a salt of ortho-nitrophenyhnitromethane with a permanganate.
- a process for the manufacture of orthonitrobeny aldehyde comprising treatment of a neutral or approximately neutral solution of a salt of ortho-nitrophenyl-nitromethane with a permanganate, in presence of a substance capable of reacting with liberated alkali to prevent detrimental action thereof.
- a process for the manufacture of orthoiitrobenzaldehyde comprising treatment of a neutral or'approximately neutral solution of a salt of ortho-nitrophenyl-nitromethane with a permanganate, in presence of mag nesium sulfate, substantially as described.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
UNITED STATES PATNT oEEroE JosEPH KOETSCHET, OF LYON, AND ANDRE BAR-BIKER, or sit. FONS, NEAR LYON,
FRANCE, ASSIGNOIRS TO sooIE'rE CHIMIQUE DES UsINEs Du nHoNE, ANCIENNE- MENT GILLIARD, P. MONNET ET CAR-TIER, or rams, FRANCE, A CORPORATION 01 MANUFACTURE OF ORTHONITROBENZALDEHYDEQ Patented July 11, 1911.
FRANCE.
997,301. Specification of Letters Patent.
No Drawing.
solutions of the salts of nitro-phenyl-nitro' methane, the. formation of nitro-benzaldehyde takes place smoothly. If care is taken that the reaction liquid remains always neutral or only Very weakly alkaline, it is possible to obtain almost theoretical yields. This is the more remarkable, as oxidation with permanganate usually yields only acids and no aldehydes.
Example: A dilute solution of QOl grams of the sodium salt of ortho-nitrophenyl nitromethane in 2000 cc. water is mixed at a low temperature with a cold solution of 105 grams permanganate of potassium (theoretical proportion) in 3000 cc. of water, and thoroughly stirred The format-ion of ortho-nitrobenzaldehyde occurs almost immediately, in accordance with the formula:
Application filed October 7, 1910.
Serial No. 585,774.
Still better yields can be obtained by adding to the permanganate solution such a quantity of magnesium 1' sulfate that the detrimentally acting alkali liberated is replaced by magnesia, which has no injurious action. Instead of magnesium sulfate. other salts giving a similar result may be employed.
lVhat we claim-and desire to secure by Letters Patent is 1.. A process for the manufacture of orthonitrobenzaldehyde, comprising treatment of a neutral or approximately neutral solution of a salt of ortho-nitrophenyhnitromethane with a permanganate.
2. A process for the manufacture of orthonitrobeny aldehyde, comprising treatment of a neutral or approximately neutral solution of a salt of ortho-nitrophenyl-nitromethane with a permanganate, in presence of a substance capable of reacting with liberated alkali to prevent detrimental action thereof.
3. A process for the manufacture of orthoiitrobenzaldehyde comprising treatment of a neutral or'approximately neutral solution of a salt of ortho-nitrophenyl-nitromethane with a permanganate, in presence of mag nesium sulfate, substantially as described.
4. A process for the manufacture of orthonitrobenzaldehydefcomprising treatment of a neutral or'approximately neutral solution of sodium salt of ortho-nitro-phenylnitro methane with a permanganate, in presence of magnesium. sulfate, substantially as described.
In witness whereof, we have hereunto signed our names in the presence of two subscribing witnesses.
JOSEPH KOETSCHET. ANDRE BARRIER.
lVitnesses 7. E. lVATTs, GUILLoT CLAUDE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58577410A US997301A (en) | 1910-10-07 | 1910-10-07 | Manufacture of orthonitrobenzaldehyde. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58577410A US997301A (en) | 1910-10-07 | 1910-10-07 | Manufacture of orthonitrobenzaldehyde. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US997301A true US997301A (en) | 1911-07-11 |
Family
ID=3065632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US58577410A Expired - Lifetime US997301A (en) | 1910-10-07 | 1910-10-07 | Manufacture of orthonitrobenzaldehyde. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US997301A (en) |
-
1910
- 1910-10-07 US US58577410A patent/US997301A/en not_active Expired - Lifetime
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